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17-keto-4(Z),7(Z),10(Z),13(Z),15(E),19(Z)-Docosahexaenoic Acid Exclusive

Cayman Chemical Item Number 9000346

17-keto-(4Z,7Z,10Z,13Z,15E,19Z)-DHA

17-keto-4(Z),7(Z),10(Z),13(Z),15(E),19(Z)-Docosahexaenoic Acid

See more	Fatty Acids (272)

Description

DHA is an essential fatty acid and the most abundant ω-3 fatty acid in neural tissues, especially in the retina and brain.17-keto-(4Z,7Z,10Z,13Z,15E,19Z) docosahexaenoic acid is a metabolite of lipoxygenase-mediated oxidation of DHA that is produced endogenously by aspirin-enhanced COX-2 activity.^1,2,3 It has been shown to activate Nrf2-dependent antioxidant gene expression, to act as a PPARγ agonist (EC₅₀ ~200nM), and to inhibit pro-inflammatory cytokine and nitric oxide production at biological concentration ranges (5-25 µM).³

1 Butovich, I.A. A one-step method of 10,17-dihydro(pero)xydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid synthesis by soybean lipoxygenase. J Lipid Res 47 854-863 (2006).

2 Jie, M.S.F.L.K., and Pasha, M.K. Fatty acids, fatty acid analogues and their derivatives. Nat Prod Rep 607-629 (1998).

3 Groeger, A.L., Cipollina, C., Cole, M.P., et al. Cyclooxygenase-2 generates anti-inflammatory mediators from omega-3 fatty acids. Nat Chem Biol (2010).

Synonyms	17-keto-(4Z,7Z,10Z,13Z,15E,19Z)-DHA
Formal Name	4Z,7Z,10Z,13Z,15E,19Z-17-keto-docosapentaenoic acid
Molecular Formula	C₂₂H₃₀O₃
Formula Weight	342.5
Formulation	A solution in ethanol
Purity	≥98%
Stability	6 months
Storage	-80°C
Shipping	Dry ice in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard CC/C=C\CC(=O)/C=C\C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O

Background Reading

Groeger, A.L., Cipollina, C., Cole, M.P., et al. Cyclooxygenase-2 generates anti-inflammatory mediators from omega-3 fatty acids. Nat Chem Biol (2010).

Jie, M.S.F.L.K., and Pasha, M.K. Fatty acids, fatty acid analogues and their derivatives. Nat Prod Rep 607-629 (1998).

Butovich, I.A. A one-step method of 10,17-dihydro(pero)xydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid synthesis by soybean lipoxygenase. J Lipid Res 47 854-863 (2006).

Size	Global Purchasing
25 µg	See a distributor in your region for pricing
50 µg	See a distributor in your region for pricing
100 µg	See a distributor in your region for pricing
250 µg	See a distributor in your region for pricing

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